期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2011, 期 4, 页码 740-750出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201001263
关键词
Natural products; Alkaloids; Cycloaddition; Azomethine ylides; Ylides
资金
- Department of Science and Technology (DST), New-Delhi
- Council of Scientific and Industrial Research (CSIR), New Delhi
Vicinal quaternary and tertiary stereocenters of the 5,10b-phenanthridine skeleton 1 are constructed simultaneously in one step by the [3+2]-cycloaddition of non-stabilized azomethine ylide 9, generated by sequential double desilylation of 10 utilizing silver(I) fluoride as a one-electron oxidant. The regioas well as stereochemical origin of this cycloaddition reaction is explained through a favorable transition state 9. The strategy is successfully applied for the total synthesis of the biologically active alkaloids (+/-)-maritidine (1a), (+/-)-crinine (1b), and their analogues (1d, 1e, and 1f).
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